first look

Our Flag Means Death Season 2: Exclusive First Look

Vanity Fair joins Stede, Blackbeard, and the rest of the cast on set in New Zealand for an exclusive early look at the second season, debuting on Max in October.
Returning cast members include Matthew Maher as Black Pete Samba Schutte as Roach Rhys Darby as Stede Samson Kayo as...
Returning cast members include Matthew Maher as Black Pete, Samba Schutte as Roach, Rhys Darby as Stede, Samson Kayo as Oluwande, and Kristian Nairn as Wee John.By Nicola Dove/Max.

Only the fans of Our Flag Means Death can determine whether they’ll be satisfied with the show’s second season, which debuts on Max in October. But if you ask Fernando Frias, who directed three of the season’s episodes, he sounds pretty confident: “If my life depended on saying whether it’s yes or no, I would say yes.’’

It’s December 8, 2022, and the principal actors on Our Flag Means Death as well as the 800-plus extras and crew members have three days left of their three-month shoot for season two. Things are starting to get emotional. “You’ve been the most amazing crew I’ve ever worked with,” says one actor as he wraps his final scene. Frias says it’s like leaving “a long summer camp,” adding, “it’s like a family.”

Rhys Darby as Stede Bonnet.Courtesy of Nicola Dove/Max.

The series created by David Jenkins was a surprise breakout hit when it debuted in the spring of 2022, building a fiercely devoted fan base with its silly yet emotional deadpan, and defiantly queer take on the adventures of real 18th-century pirates. Everyone involved in Our Flag Means Death is eager to preserve the surprises in store for season two, which kicks off with gentleman pirate Stede Bonnet (Rhys Darby) and softhearted bad boy Blackbeard (Taika Waititi) ruefully separated after finally realizing their love for each other at the end of season one. It’s “going to be unexpected and surprising, but also very pleasurable and satisfying for those who like the show,” promises executive producer Garrett Basch. It “doesn’t follow the expected route,” teases Con O’Neill, who plays Blackbeard’s devoted enforcer, Izzy. All that means is we’re not at liberty to share too much about what happened on set that day, which included emotional conversations, new cast members, banter with the Kiwi crew, and some seriously killer costumes.

But these exclusive new images give a hint of what is in store. There are fresh faces—Minnie Driver will guest-star as the real-life Irish pirate Anne Bonny, and Ruibo Qian joins the cast as the mysterious merchant Susan—and a lot of New Zealand actors and locations, now that the production has decamped across the Pacific. “The viewers will see the scope of their world has expanded based on the fact we’re able to get to these amazing locations within a short travel time,” says executive producer Antoine Douaihy. “You will notice a marked difference between the two seasons in terms of the scope and the scale.’’

Minnie Driver joins the cast this season as Anne Bonny.Courtesy of Nicola Dove/Max.

There will be plenty of familiar faces too, of course. On set that day in Kumeu, New Zealand, a rural area about 20 miles outside of Auckland, are Waititi and Darby along their fellow returning cast members O’Neill, Vico Ortiz (Jim), Kristian Nairn (Wee John), Joel Fry (Frenchie), Matthew Maher (Black Pete), Leslie Jones (Spanish Jackie), Samson Kayo (Oluwande), Ewen Bremner (Nathaniel Buttons), Samba Schutte (Roach), and more. New onboard are two Kiwi actors, Madeleine Sami (most recently of the Australian mystery-comedy Deadloch), and Samoan-born Anapela Polataivao. And there’s one returning figure impossible to miss on the soundstage: The Revenge, the stately ship that Blackbeard—a.k.a. Ed—commandeered at the end of season one. In real life it was carefully transported across the Pacific Ocean from the show’s original Los Angeles soundstages.

The Revenge is vast and impressive, much larger in real life than it appears onscreen. But it’s not the only stunning scenery in store. There are around 50 sets involved in the production of season two, including the 30-acre forest behind the Kumeu Film Studio, Piha Beach, and the wild, black-sand Bethells Beach.

Waititi, who also executive produces the series, was part of the push to film season two in his native New Zealand. “Taika is an extraordinary talent and what’s really great about him with his international success is he’s remained very committed to New Zealand and very loyal to our industry,” says Annie Murray, the CEO of the New Zealand Film Commission. “The beauty of filming in New Zealand is that you can find incredible varied locations within a very short driving distance. [And] when you get to those locations you can turn your camera in any direction.’’

Rhys Darby as Stede Bonnet, filming at New Zealand’s Bethells Beach.Courtesy of Nicola Dove/Max.

The scope of the season is very evident back on set, as well. There’s a whole other pirate ship in addition to The Revenge, plus sets for a floating market, Stede’s cabin (empty when we visit), and the Republic of Pirates first glimpsed in season one. Behind the scenes it’s a maze of wardrobe, wig rooms, and dressing rooms. In another facility, props are stacked on shelves, ready to be taken away to storage as soon as filming wraps—vases, plates, antique furniture, and piles of mannequins replicating dead bodies which were used in one of the battle scenes.

Costume designer Gypsy Taylor joined the production this season and has designed hundreds of costumes, checking with everyone on set that day to make sure everything is in place before cameras roll. Taylor says each of the principals have six to eight looks in this season, and that every item—every leather belt, wig, bit of jewelry, even a mermaid tail—has been made by her 60-strong workshop. The costumes this season have a “Mad Max, ‘streets of New York’ feel,” says Taylor. “David Jenkins was keen to give the series a cool rock-and-roll vibe…so we had these rock-and-roll elements with an 18th-century twist.’’ As is evidenced in the image below, even Stede’s crew winds up with some unexpected new looks over the course of the season.

Wherever it is these Revenge crew members have found themselves, there’s something that surprised them.Courtesy of Nicola Dove/Max.

Two armies are part of the action in season two, all of them needing elaborate costumes—around 150 Chinese pirates and a fleet of 100 navy officers. Even the breeches are in studded black leather, and punkified. Says Taylor, “The theory behind their costumes is they would’ve stolen from other pirates…. Although our Wee John has started to become quite the seamstress, so he’s knitting this season.’’ True enough: Nairn is wearing what looks like a hand-knit sweater on set that day.

Wee John isn’t the only pirate getting into crafts. Nancy Hennah, who has managed the hair and makeup for both seasons, points to Blackbeard’s wig—made in London—and tattoos as Waititi works on set. With 14 tattoos on his right arm and 10 on the left, plus plenty of scars, he needs at least an hour in the makeup chair. “Taika wanted most of the tattoos to look like he’d done them himself,” Hennah says. “Like on slow days on the boat when there’s nothing much to do, they sit around and give each other tattoos.”

She gives a hint of a storm in one episode: “One of the hardest days here in makeup was when they were caught in a storm on the back of the boat. [The cast] were saturated for a whole day, which caused havoc with things like tattoos and hair, wigs and beards.’’

Taika Waititi as Blackbeard, who begins the season with a broken heart.Courtesy of Nicola Dove/Max.

By mid afternoon, Con O’Neill is taking a break in his trailer. He pulls his slim, leather-trousered legs up to a corner seat. A candle blazes on the kitchen bench as the veteran actor talks about the physical endurance required during the shoot. “It’s been frantic,’’ he says. His signature gray hair barely moves, frozen by the team of hairstylists who arrived on set around sunrise. (All interviews with actors in this story took place before the SAG-AFTRA strike.) 

Izzy “goes on a remarkable journey” this season, says O’Neill. “He understands what love is and whom he’s in love with.’’ On a series featuring a variety of joyful queer relationships—not just Stede and Blackbeard, but Black Pete and Lucius (Nathan Foad), Jim and Oluwande, and Spanish Jackie and her many husbands—Izzy’s unyieldingly straitlaced devotion makes him an odd man out. By the end of season one many fans speculated that Izzy was driven by something at the intersection of love and obsession. This season, according to O’Neill, Izzy gets even deeper into that dynamic. “Physically it’s been quite demanding, and also emotionally it’s been quite demanding to be playing a man enraged by unrequited love, who’s basically a hopeless romantic, and to be able to play all that and also remember that this is fundamentally a comedy.’’

Though the show is often warm and fuzzy when it comes to feelings—one of Stede’s mottos in season one is that when faced with challenges, “we talk it through as a crew”—Izzy represents the darker, more violent side of pirate life, which the show doesn’t shy away from either. “What I love about this show is it does allow itself to swing between the two,” O’Neill says. “We’re almost operatic in our darkness at times, and then we swing back to the sweetness of the simplicity of the love of our two guys. It’s been challenging just to get the tone right.”

“We’ve gone further this season than we did last season with those tones,” he continues. “So sometimes it’s quite interesting to remind yourself that you have to take your foot out of the tragedy—literally, your foot—and put it back into the comedy.”

With a season behind them to build the dynamics between the characters and the actors alike, on set there’s been “a lot more spontaneity and script revisions based on what’s happening day-to-day,” says Douaihy. “The cast are so comfortable with one another and their characters, that they move through it naturally.’’

Leslie Jones as Spanish Jackie and Taika Waititi as Ed a.k.a. Blackbeard.Courtesy of Nicola Dove/Max.

The way O’Neill puts it, they’ve also built trust with Jenkins, their showrunner, to follow some bigger swings. “I don’t think David Jenkins is ever going to follow an expected route. I’d hate to drive in a car with him.” Thinking of the fans who will greet the series when the show returns in October, O’Neill continues, “I think they’re going to appreciate what [Jenkins] wants. Season two does stick to the original premise that we created in season one, which is take it on to other levels.’’

One character leveling up in a major way this season is Jim, the quiet badass (there are knives involved) played by the nonbinary actor and activist Vico Ortiz. “Jim really evolves in season two,” they say. “They’re a bit more chatty and a bit more conversational…. Most of the first season you see Jim in disguise, hiding, but in this one you see them a bit more [thinking,] Oh, this is my chosen family, and I feel good. There’s a bit more zaniness and a bit more softness.’’

Like O’Neill and several other castmates, Oritz had attended their share of fan events by the time season two began filming, and the entire cast and crew returned to the high seas with a strong sense that their show had taken on a life of its own. “It’s so beautiful to see that people are finding community within the fan base. It’s about creating spaces where we feel safe and seen, and it’s so great to see that so many people watch the show and feel validated in their experiences, whatever that may be,” says Ortiz. “A lot of people that watch the show are like, “Yeah, I’m a guy and it’s good to see all these dudes being vulnerable.’ We can just shake up [ideas about gender].’’

Ruibo Qian joins the cast this season as Susan, a merchant with secrets of her own.Courtesy of Nicola Dove/Max.

Basch admits the fan following surprised some of the team, “but it made a lot of sense” too. After years of television shows and movies that built up the potential of queer romance only to stop short, Basch thinks the fervor for Our Flag Means Death “says that shows in the mainstream aren’t delivering that promise or that setup, and we have. That’s really why the fans have gone wild for it.”

That promise, it’s safe to say, is kept in season two, and then some. On set that day in December, for example, there was a major romantic moment between two key characters. But we’d risk Ed Teach’s wrath if we told you any more.